Diving Deep with Subscript

A video series where we dive deep and explore SaaS metrics with leading investors, CEOs, and finance leaders

Episodes

Episode 25

August 22, 2025
A conversation with Matt Kennard, CEO of BetterLesson
In this episode of Diving Deep, Subscript's CEO, Sidharth Kakkar is joined by Matt Kennard, CEO of BetterLesson. They discuss Matt's transition from CFO to CEO, his operator-first approach to finance, M&A lessons from both sides of the table, and more.
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Episode 24

June 27, 2025
A conversation with Kareem Amin, Co-founder and CEO of Clay
In this episode of Diving Deep, Subscript's CEO, Sidharth Kakkar, sits down with Kareem Amin, Co-founder and CEO of Clay. They discuss Clay's co-founder dynamic, the learnings from Clay's first rollout of usage-based pricing, Kareem's fundraising mindset that led to multiple preempted rounds, the team's approach to headcount planning, and more!
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Episode 23

April 24, 2025
A conversation with Amy Kalnoki, Co-Founder and COO of Bitwave
In this episode of Diving Deep, Subscript's CEO, Sidharth Kakkar, is joined by Amy Kalnoki, Co-Founder and COO of Bitwave. They discuss what CFOs should understand about digital assets, emerging enterprise use cases for crypto, why wallet hygiene is critical, where traditional ERPs fall short with crypto, and much more!
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Episode 22

April 4, 2025
A conversation with Waseem Daher, Founder and Executive Chair of Pilot
In this episode of Diving Deep, Subscript's CEO, Sidharth Kakkar, is joined by Waseem Daher, Founder and Executive Chair of Pilot. They discuss how CFOs can build credibility as business leaders, when to embrace creativity as a finance leader, why you need a new playbook for fundraising in 2025, and much more!
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Episode 21

February 6, 2025
A conversation with Ruchi Kasliwal, VP Finance + Ops at Zededa
In this episode of Diving Deep, Subscript's CEO, Sidharth, has an engaging conversation with Ruchi Kasliwal, VP Finance + Ops at Zededa. Ruchi discusses GenAI, the changing role of finance, balancing headcount and technology investments, the partnership between RevOps and Finance, and more!
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Episode 20

November 15, 2024
A conversation with Madhu Jagannathan, CFO at Lob
In this episode of Diving Deep, Subscript's CEO, Sidharth, has an engaging conversation with Madhu Jagannathan, CFO at Lob. Madhu discusses usage-based billing, why the Deal Desk should report to finance, and much more!
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Episode 19

December 17, 2024
A conversation with Sam Bonning, VP Finance & Strategy at Remote
In this episode of Diving Deep, Subscript's CEO, Sidharth, has an engaging conversation with Sam Bonning, VP Finance & Strategy at Remote. Sam discusses strategic planning, how to successfully work with founders, and much more!
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Episode 18

September 20, 2023
A conversation with Conor O'Donoghue, CFO at Ocrolus
In this episode of Diving Deep, we’re joined by Conor O'Donoghue, CFO at Ocrolus. Conor discusses handling the financial complexities of a usage-based business, how to ensure your finance team has the right tools and skills for 2023, and much more!
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Episode 17

September 20, 2023
A conversation with Karen Moran, CFO at H1
In this episode of Diving Deep, we’re joined by Karen Moran, CFO at H1. Karen shares why finance teams need to "think big and build bigger" when it comes to systems, people, and processes. She also offers thoughtful advice for navigating an economic downturn.
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Episode 16

September 20, 2023
A conversation with Isabelle Winkles, CFO at Braze
In this episode of Diving Deep, we’re joined by Isabelle Winkles, CFO at Braze. Isabelle shares her advice for navigating a challenging economy, a thoughtful approach to adding to your finance tech stack, and much more!
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Episode 15

September 20, 2023
A conversation with Rose Punkunus, CEO at Sudozi
In this episode of Diving Deep, we’re joined by Rose Punkunus, CEO at Sudozi. In addition to her brilliant work at Sudozi, Rose was also the CFO of Uber, and a Data Science and Analytics Lead for Apple. Without a doubt, Rose is one of the most data-driven (and talented) finance leaders that you'll ever meet.
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Episode 14

September 20, 2023
A conversation with Rajeev Dham, Partner at Sapphire Ventures
In this episode of Diving Deep, we’re joined by Rajeev Dham, Partner at Sapphire Ventures. Rajeev discusses the two traits that set the greatest CFOs apart, concrete advice for navigating an uncertain economy, and a lot more!
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Episode 13

September 20, 2023
A conversation with Mark Khavkin, CFO at Pantheon
In this episode of Diving Deep, we’re joined by Mark Khavkin, CFO at Pantheon. Mark discusses the art and science of uncovering strategic insights from SaaS metrics, how to forecast revenue when there's economic uncertainty, and a lot more!
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Episode 12

September 20, 2023
A conversation with Mohit Daswani, CFO at ThoughtSpot
We’re joined by Mohit Daswani, CFO at ThoughtSpot, who discusses the importance of segmenting your SaaS metrics, the benefits of building a data-driven culture, and a lot more!
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Episode 11

September 20, 2023
A conversation with Paul Barnhurst, Founder of The FP&A Guy
We’re joined by Paul Barnhurst, Founder at The FP&A Guy who discusses when finance teams should say goodbye to Excel, 4 key pillars of FP&A planning tools, and a lot more!
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Episode 10

September 20, 2023
A conversation with Michael Tam, Partner at Craft Ventures
In this episode of Diving Deep, we’re joined by Michael Tam, Partner at Craft Ventures. Michael discusses the three categories of metrics that investors care about, B2B SaaS benchmarks to focus on when you're prioritizing efficiency, and a lot more!
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Episode 09

September 20, 2023
A conversation with Alka Tandan, CFO at Gainsight
In this episode of Diving Deep, we’re joined by Alka Tandan, CFO at Gainsight. Alka discusses the key levers for increasing NRR, the increased importance of customer success when times are tough, and a lot more!
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Episode 08

September 20, 2023
A conversation with Todd Gardner, Managing Director at SaaS Advisors
In this episode of Diving Deep, Subscript's CEO, Sidharth, has an engaging conversation with Todd Gardner, Managing Director at SaaS Advisors. They discuss the pros and cons of usage-based pricing, why you need to look at retention by product line, and a lot more!
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Episode 07

September 20, 2023
A conversation with Mike DePaschalis, Head of Finance at Postal.io
In this episode of Diving Deep, we’re joined by Mike DePaschalis, Head of Finance at Postal.io. Mike discusses the downsides of keeping your subscription metrics in Excel, what you can learn by looking at cohorts of your customers, and more!
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Episode 06

September 20, 2023
A conversation with Chitra Balasubramanian, CFO at CircleCI
In this episode of Diving Deep, Subscript's CEO, Sidharth, is joined by Chitra Balasubramanian, CFO at CircleCI. They discuss why strategic finance leaders need to double-click into their SaaS metrics, one critical piece of advice for companies adding usage-based pricing, and a lot more!
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Episode 05

September 20, 2023
A conversation with Kyle Poyar, Operating Partner at OpenView
In this episode of Diving Deep, Subscript's CEO, Sidharth, has an engaging conversation with Kyle Poyar, Operating Partner at OpenView. They discuss what finance teams need to know about usage-based pricing, two mistakes to avoid when calculating LTV:CAC, how to pick the right NDR benchmark, and a lot more!
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Episode 04

September 20, 2023
A conversation with Frank Bien, former President and CEO at Looker
In this episode of Diving Deep, we’re joined by the brilliant Frank Bien, former President and CEO of Looker. Frank discusses concrete advice for operating in an economic downturn, tips for avoiding a “data brawl,” and a lot more!
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Episode 03

September 20, 2023
A conversation with Tien Anh Nguyen, former CFO at UserTesting
In this episode of Diving Deep, Subscript's CEO, Sidharth, is joined by Tien Anh Nguyen, former CFO and Chief Business Officer at UserTesting. They discuss advice for presenting subscription metrics to VCs, the #1 pain point for all CFOs, and a lot more!
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Episode 02

September 20, 2023
A conversation with Kristina Shen from Andreessen Horowitz
In this episode of Diving Deep, Subscript's CEO, Sidharth, is joined by Kristina Shen, General Partner at Andreessen Horowitz. They discuss the dangers of measuring LTV, why The Rule of 40 isn't good enough, and a lot more!
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Episode 01

September 20, 2023
A conversation with Tomasz Tunguz from Redpoint Ventures
In this episode of Diving Deep, Subscript's CEO, Sidharth, has an engaging conversation with Tomasz Tunguz, Managing Director at Redpoint Ventures. They discuss the key SaaS metrics Tomasz needs to see when evaluating a company, why NDR might be even more important than you first thought, and a lot more!
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